Product Name

  • Name

    Tacalcitol

  • EINECS
  • CAS No. 57333-96-7
  • Article Data9
  • CAS DataBase
  • Density 1.06 g/cm3
  • Solubility
  • Melting Point
  • Formula C27H44O3
  • Boiling Point 565 °C at 760 mmHg
  • Molecular Weight 416.645
  • Flash Point 238.4 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes R50/53; R33; R26/27/28
  • Molecular Structure Molecular Structure of 57333-96-7 (Tacalcitol)
  • Hazard Symbols N,T+
  • Synonyms 1a,24R-Dihydroxyvitamin D3;Bonalfa;Curatoderm;PRI 2191;TV 02;9,10-Secocholesta-5,7,10(19)-triene-1,3,24-triol,(1a,3b,5Z,7E,24R)- (9CI);1a,24(R)-Dihydroxycholecalciferol;
  • PSA 60.69000
  • LogP 5.56060

Synthetic route

((1R,3S,Z)-5-((E)-2-((1R,7aR)-7a-methyl-1((2R,5R)-6-methyl-5-(triethylsilyloxy)heptan-2-yl)dihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diyl)bis(oxy)bis(tert-butyldimethylsilane)

((1R,3S,Z)-5-((E)-2-((1R,7aR)-7a-methyl-1((2R,5R)-6-methyl-5-(triethylsilyloxy)heptan-2-yl)dihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diyl)bis(oxy)bis(tert-butyldimethylsilane)

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; Darkness;98%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 40h; Darkness;98%
(1R,3S)-5-[2-[(1R,3aS,7aR)-1-((1R,4R)-4-Methoxymethoxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexane-1,3-diol

(1R,3S)-5-[2-[(1R,3aS,7aR)-1-((1R,4R)-4-Methoxymethoxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexane-1,3-diol

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
With hydrogen fluoride In water; acetonitrile at 20℃; for 24h;76%
With methanol; AG 50W-X4 resin at 20℃; methanolysis;33 mg
C41H74O4Si2

C41H74O4Si2

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Stage #1: C41H74O4Si2 With potassium carbonate In methanol at 20℃; for 5h;
Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran for 2h; Reflux;		75%
C46H76O4Si2

C46H76O4Si2

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Stage #1: C46H76O4Si2 With potassium carbonate In methanol at 20℃; for 5h;
Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran for 2h; Reflux;		75%
C39H72O3Si2

C39H72O3Si2

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
With (1S)-10-camphorsulfonic acid In methanol; chloroform at 20℃; for 2.5h;65%
Stage #1: C39H72O3Si2 With tetrabutyl ammonium fluoride In tetrahydrofuran at 50 - 55℃; for 2h;
Stage #2: With maleic anhydride In ethyl acetate at 30 - 35℃; for 24h;		300 mg
1α,3β,24(R)-trihydroxycholesta-5,7-diene
57701-47-0

1α,3β,24(R)-trihydroxycholesta-5,7-diene

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
In diethyl ether Irradiation;
(S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate
66774-80-9

(S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: 91 percent / dimethylsulfoxide / 2 h / 90 °C
2.1: 98 percent / imidazole / dimethylformamide / 12 h / 80 °C
3.1: lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -78 - 0 °C
3.2: 91 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 7 h / -60 - 20 °C
4.1: 94 percent / tert-butanol; potassium; hexamethylphosphoramide / diethyl ether / 13 h / 0 - 20 °C
5.1: 93 percent / N,N-diisopropylethylamine / CH2Cl2 / 0 - 20 °C
6.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating
7.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C
8.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C
8.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C
9.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C
10.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
11.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
12.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
13.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C
View Scheme
(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol
64190-52-9

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1.1: 93 percent / pyridine / 12 h / 0 °C
2.1: 91 percent / dimethylsulfoxide / 2 h / 90 °C
3.1: 98 percent / imidazole / dimethylformamide / 12 h / 80 °C
4.1: lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -78 - 0 °C
4.2: 91 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 7 h / -60 - 20 °C
5.1: 94 percent / tert-butanol; potassium; hexamethylphosphoramide / diethyl ether / 13 h / 0 - 20 °C
6.1: 93 percent / N,N-diisopropylethylamine / CH2Cl2 / 0 - 20 °C
7.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating
8.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C
9.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C
9.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C
10.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C
11.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
12.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
13.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
14.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C
View Scheme
Multi-step reaction with 11 steps
1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 96 h / 20 °C
2: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C
3: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 12 h / 0 - 20 °C
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C
5: lithium hexamethyldisilazane / tetrahydrofuran / 15 h / -78 - 20 °C
6: tetrabutyl ammonium fluoride / tetrahydrofuran / 17 h / 65 °C
7: hydrogen; palladium 10% on activated carbon / methanol / 15 h
8: dipyridinium dichromate / dichloromethane / 20 °C
9: n-butyllithium / tetrahydrofuran / 18 h / -78 °C
10: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Darkness
11: hydrogen fluoride / acetonitrile; water / 24 h / 20 °C
View Scheme
Multi-step reaction with 10 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 50 - 55 °C
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / -5 - 5 °C
3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide; sodium hypochlorite; sodium hydrogencarbonate / dichloromethane; water / 0.17 h / -5 - 5 °C
4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -70 - -60 °C
4.2: -70 - 20 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 55 - 60 °C
6.1: pyridinium chlorochromate / dichloromethane / 20 °C
7.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 24 h / 2280.15 - 2660.18 Torr
8.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C
9.1: n-butyllithium / tetrahydrofuran / 1 h / -70 - -60 °C
9.2: 1.5 h / -65 - -10 °C
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Darkness
View Scheme
Multi-step reaction with 10 steps
1.1: 1H-imidazole; ammonium chloride / N,N-dimethyl-formamide / 50 - 55 °C / Inert atmosphere
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 4 h / 20 °C / Inert atmosphere
4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -70 °C / Inert atmosphere
4.2: -70 - 20 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 60 °C / Inert atmosphere
6.1: dipyridinium dichromate / dichloromethane / 20 °C
7.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 24 h / 2280.15 - 2660.18 Torr
8.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
9.1: n-butyllithium / tetrahydrofuran / 1 h / -65 °C / Inert atmosphere
9.2: 1.5 h / -65 - -10 °C / Inert atmosphere
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 40 h / 20 °C / Darkness
View Scheme
<1R-<1β(R*),3aα,4β,7aβ>>-octahydro-4-hydroxy-β,7a-dimethyl-1H-indene-1-propanenitrile
93489-60-2

<1R-<1β(R*),3aα,4β,7aβ>>-octahydro-4-hydroxy-β,7a-dimethyl-1H-indene-1-propanenitrile

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: 98 percent / imidazole / dimethylformamide / 12 h / 80 °C
2.1: lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -78 - 0 °C
2.2: 91 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 7 h / -60 - 20 °C
3.1: 94 percent / tert-butanol; potassium; hexamethylphosphoramide / diethyl ether / 13 h / 0 - 20 °C
4.1: 93 percent / N,N-diisopropylethylamine / CH2Cl2 / 0 - 20 °C
5.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating
6.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C
7.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C
7.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C
8.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C
9.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
10.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
11.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
12.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C
View Scheme
De-A,B-(24R)-8β-[(tert-butyldimethylsilyl)oxy]-cholestan-24-ol
145223-31-0

De-A,B-(24R)-8β-[(tert-butyldimethylsilyl)oxy]-cholestan-24-ol

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 93 percent / N,N-diisopropylethylamine / CH2Cl2 / 0 - 20 °C
2.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating
3.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C
4.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C
4.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C
5.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C
6.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
7.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
8.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
9.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C
View Scheme
(R)-3-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)butanenitrile
145223-29-6

(R)-3-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)butanenitrile

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -78 - 0 °C
1.2: 91 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 7 h / -60 - 20 °C
2.1: 94 percent / tert-butanol; potassium; hexamethylphosphoramide / diethyl ether / 13 h / 0 - 20 °C
3.1: 93 percent / N,N-diisopropylethylamine / CH2Cl2 / 0 - 20 °C
4.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating
5.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C
6.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C
6.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C
7.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C
8.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
9.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
10.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
11.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C
View Scheme
De-A,B-(24R,22ξ)-8β-[(tert-butyldimethylsilyl)oxy]-24-hydroxy-cholestane-22-carbonitrile
145223-30-9

De-A,B-(24R,22ξ)-8β-[(tert-butyldimethylsilyl)oxy]-24-hydroxy-cholestane-22-carbonitrile

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: 94 percent / tert-butanol; potassium; hexamethylphosphoramide / diethyl ether / 13 h / 0 - 20 °C
2.1: 93 percent / N,N-diisopropylethylamine / CH2Cl2 / 0 - 20 °C
3.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating
4.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C
5.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C
5.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C
6.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C
7.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
8.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
9.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
10.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C
View Scheme
De-A,B-(24R)-24-[(methoxymethyl)oxy]-cholestan-8-one
188949-00-0

De-A,B-(24R)-24-[(methoxymethyl)oxy]-cholestan-8-one

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C
1.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C
2.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C
3.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
4.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
5.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
6.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: n-butyllithium / tetrahydrofuran / 18 h / -78 °C
2: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Darkness
3: hydrogen fluoride / acetonitrile; water / 24 h / 20 °C
View Scheme
De-A,B-(24R)-8β-hydroxy-cholestan-24-ol methoxymethyl ether
188948-99-4

De-A,B-(24R)-8β-hydroxy-cholestan-24-ol methoxymethyl ether

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C
2.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C
2.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C
3.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C
4.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
5.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
6.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
7.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: dipyridinium dichromate / dichloromethane / 20 °C
2: n-butyllithium / tetrahydrofuran / 18 h / -78 °C
3: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Darkness
4: hydrogen fluoride / acetonitrile; water / 24 h / 20 °C
View Scheme
De-A,B-(24R)-24-[(methoxymethyl)oxy]-cholest-8-en-8-yl trifluoromethanesulfonate
188948-96-1

De-A,B-(24R)-24-[(methoxymethyl)oxy]-cholest-8-en-8-yl trifluoromethanesulfonate

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C
2: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
3: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
4: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
5: 33 mg / AG 50W-X4 resin; methanol / 20 °C
View Scheme
De-A,B-(24R)-8β-[(tert-butyldimethylsilyl)oxy]-cholestan-24-ol methoxymethyl ether
188948-98-3

De-A,B-(24R)-8β-[(tert-butyldimethylsilyl)oxy]-cholestan-24-ol methoxymethyl ether

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating
2.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C
3.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C
3.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C
4.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C
5.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
6.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
7.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
8.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C
View Scheme
(24R)-1α-[(tert-butyldimethylsilyl)oxy]-6,7-didehydro-24-[(methoxymethyl)oxy]-previtamin D3 tert-butyldimethylsilyl ether
188948-95-0

(24R)-1α-[(tert-butyldimethylsilyl)oxy]-6,7-didehydro-24-[(methoxymethyl)oxy]-previtamin D3 tert-butyldimethylsilyl ether

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
2: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
3: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
4: 33 mg / AG 50W-X4 resin; methanol / 20 °C
View Scheme
1α-[(tert-butyldimethylsilyl)oxy]-24R-[(methoxymethyl)oxy]-previtamin D3 tert-butyldimethylsilyl ether
188949-01-1

1α-[(tert-butyldimethylsilyl)oxy]-24R-[(methoxymethyl)oxy]-previtamin D3 tert-butyldimethylsilyl ether

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
2: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
3: 33 mg / AG 50W-X4 resin; methanol / 20 °C
View Scheme
1α-[(tert-butyldimethylsilyl)oxy]-24R-[(methoxymethyl)oxy]-vitamin D3 tert-butyldimethylsilyl ether
188949-02-2

1α-[(tert-butyldimethylsilyl)oxy]-24R-[(methoxymethyl)oxy]-vitamin D3 tert-butyldimethylsilyl ether

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
2: 33 mg / AG 50W-X4 resin; methanol / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Darkness
2: hydrogen fluoride / acetonitrile; water / 24 h / 20 °C
View Scheme
1α, 3β, 24-trihydroxycholest-5-ene
59780-19-7

1α, 3β, 24-trihydroxycholest-5-ene

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Py
3: diethyl ether / Irradiation
View Scheme
1α, 2α-epoxy-24-keto-cholesta-4,6-dien-3-one
57701-42-5

1α, 2α-epoxy-24-keto-cholesta-4,6-dien-3-one

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Li, NH4Cl, liq. NH3
2: Py
4: diethyl ether / Irradiation
View Scheme
1α-Hydroxy-3β,24(R)-dibenzoyloxy-cholest-5-ene
57333-97-8

1α-Hydroxy-3β,24(R)-dibenzoyloxy-cholest-5-ene

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: diethyl ether / Irradiation
View Scheme
C24H46O2Si

C24H46O2Si

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere
2.1: palladium on activated charcoal; hydrogen / methanol / 760.05 Torr
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 10 h / Reflux
4.1: pyridinium dichromate; aluminum oxide / dichloromethane / 20 h / 20 °C
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -60 °C / Inert atmosphere
5.2: 2 h / 20 °C
6.1: potassium carbonate / methanol / 5 h / 20 °C
6.2: 2 h / Reflux
View Scheme
C34H50O2Si

C34H50O2Si

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: pyridine / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere
2.1: palladium on activated charcoal; hydrogen / methanol / 760.05 Torr
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 10 h / Reflux
4.1: pyridinium dichromate / dichloromethane / 20 h / 20 °C / Inert atmosphere
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -60 °C / Inert atmosphere
5.2: 2 h / 20 °C
6.1: potassium carbonate / methanol / 5 h / 20 °C
6.2: 2 h / Reflux
View Scheme
C26H48O3Si

C26H48O3Si

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: palladium on activated charcoal; hydrogen / methanol / 760.05 Torr
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 10 h / Reflux
3.1: pyridinium dichromate; aluminum oxide / dichloromethane / 20 h / 20 °C
4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -60 °C / Inert atmosphere
4.2: 2 h / 20 °C
5.1: potassium carbonate / methanol / 5 h / 20 °C
5.2: 2 h / Reflux
View Scheme
C41H54O3Si

C41H54O3Si

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: palladium on activated charcoal; hydrogen / methanol / 760.05 Torr
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 10 h / Reflux
3.1: pyridinium dichromate / dichloromethane / 20 h / 20 °C / Inert atmosphere
4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -60 °C / Inert atmosphere
4.2: 2 h / 20 °C
5.1: potassium carbonate / methanol / 5 h / 20 °C
5.2: 2 h / Reflux
View Scheme
C26H50O3Si

C26H50O3Si

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 10 h / Reflux
2.1: pyridinium dichromate; aluminum oxide / dichloromethane / 20 h / 20 °C
3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -60 °C / Inert atmosphere
3.2: 2 h / 20 °C
4.1: potassium carbonate / methanol / 5 h / 20 °C
4.2: 2 h / Reflux
View Scheme
C41H56O3Si

C41H56O3Si

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 10 h / Reflux
2.1: pyridinium dichromate / dichloromethane / 20 h / 20 °C / Inert atmosphere
3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -60 °C / Inert atmosphere
3.2: 2 h / 20 °C
4.1: potassium carbonate / methanol / 5 h / 20 °C
4.2: 2 h / Reflux
View Scheme
C20H36O3

C20H36O3

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: pyridinium dichromate; aluminum oxide / dichloromethane / 20 h / 20 °C
2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -60 °C / Inert atmosphere
2.2: 2 h / 20 °C
3.1: potassium carbonate / methanol / 5 h / 20 °C
3.2: 2 h / Reflux
View Scheme
C25H38O3

C25H38O3

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: pyridinium dichromate / dichloromethane / 20 h / 20 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -60 °C / Inert atmosphere
2.2: 2 h / 20 °C
3.1: potassium carbonate / methanol / 5 h / 20 °C
3.2: 2 h / Reflux
View Scheme
tacalcitol
57333-96-7

tacalcitol

1α,24(R)-dihydroxy-6,19-dihydro-6,19-epidioxyvitamin D3

1α,24(R)-dihydroxy-6,19-dihydro-6,19-epidioxyvitamin D3

Conditions
ConditionsYield
With oxygen; rose bengal In ethanol for 1h; Irradiation; Yield given;

Tacalcitol Specification

1. Introduction of Tacalcitol

Tacalcitol, with  the IUPAC Name of (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R,5S)-5-Hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol, is one kind of powder. And it belongs to the Product categories which include Vitamin D3 analogs.    

2. Properties of Tacalcitol

Tacalcitol has the following properties: (1)Density: 1.06 g/cm3; (2)Flash Point: 238.4 °C; (3)Index of Refraction: 1.545; (4)Boiling Point: 565 °C at 760 mmHg; (5)Vapour Pressure: 4.05E-15 mmHg at 25°C; (6)Appearance: White solid; (7)Index of Refraction: 1.545; (8)Molar Refractivity: 124.3 cm3; (9)Molar Volume: 392.7 cm3.

3. Structure Descriptors of Tacalcitol

You could convert the following datas into the molecular structure:
(1).Canonical SMILES: CC(C)C(CCC(C)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C)O
(2).Isomeric SMILES: C[C@H](CC[C@@H](C(C)C)O)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](C
[C@@H](C3=C)O)O)C
(3).InChI: InChI=1S/C27H44O3/c1-17(2)25(29)13-8-18(3)23-11-12-24-20(7-6-14-27(23,24)5)9-10-21-15-22(28)16-26(30)19(21)4/h9-10,17-18,22-26,28-30H,4,6-8,11-16H2,1-3,5H3/b20-9+,21-10-/t18-,22-,23-,24+,25+,26+,27-/m1/s1  
(4).InChIKey: BJYLYJCXYAMOFT-SEZLTJOTSA-N

4. Toxicity of Tacalcitol

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 subcutaneous 10ug/kg (0.01mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)

BLOOD: "CHANGES IN SERUM COMPOSITION (E.G., TP, BILIRUBIN, CHOLESTEROL)"		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 17, Pg. 4615, 1989.
mouse LD50 intravenous 559ug/kg (0.559mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 17, Pg. 4615, 1989.
mouse LD50 oral 3050ug/kg (3.05mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 17, Pg. 4615, 1989.
mouse LD50 subcutaneous 419ug/kg (0.419mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 17, Pg. 4615, 1989.
rat LD50 intravenous 556ug/kg (0.556mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

SKIN AND APPENDAGES (SKIN): HAIR: OTHER		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 17, Pg. 4615, 1989.
rat LD50 oral 3279ug/kg (3.279mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 17, Pg. 4615, 1989.
rat LD50 subcutaneous 100ug/kg (0.1mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 17, Pg. 4615, 1989.
rat LD50 subcutaneous 100ug/kg (0.1mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 17, Pg. 4615, 1989.

5. Safety Information of Tacalcitol

A poison by ingestion, subcutaneous, and intravenous routes. When heated to decomposition it emits acrid smoke and irritating vapors.

6. Use of Tacalcitol

Tacalcitol (CAS NO.57333-96-7) is a durg for preventing anti-psoriasis and keratosis. It can be used for psoriasis, ichthyosis, palmoplantar keratoderma pus blisters disease and keratosis.

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